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Turning Points

September 2005 – I arrive only with what I can carry. Some well-worn and ugly luggage, a laptop bag, and a handful of garments on hangers. The rest of my stuff, not a lot of things after downsizing, sits in storage.

I arrive as so many did, with nothing to my name. No job, no money, just the hope that better life waits for me in New York. My Ellis Island is a cramped living room in Astoria. The first few weeks are a scramble, I chase down any sort of work I can find, interviewing wherever possible. I learn the subways as I go. I learn to sleep through the night on my friends’ sofa, even when their cats have other thoughts on the matter.

Six weeks into the adventure, I accept a job as part of the launch team of Top of the Rock Observation Deck at Rockefeller Center.

December 2006 – She’s leaving for Japan at the end of a long weekend. It’s been an unconventional relationship, long-distance, among other complications. But for this one weekend, this last weekend, we’re together and I can share my city with her. She’s never been here before, and I want to do it right. We see some of the sights, but the best moments are always the ones the guide books never tell you about.

She loves to cook and has been promising me she’d make her jambalaya After some research she finds a place that seems to sell quality andouie sausage. Her eyes light up as we walk into Esposito’s in Hell’s Kitchen. The smell of meat hangs in the air and it’s clear we’ve chosen well. The jambalaya is amazing, some of the best I’ve ever had, including restaurants in NOLA. The weekend is wonderful and bittersweet. Farewells are difficult and her flight from JFK will take her out of the country and out of my life.

I knew I loved New York before now, but now I know the joy of sharing it with someone I care about. New York is best when shared.

August 2007 – My 30th birthday party. I’m surrounded by friends from my personal and work lives. My life, frequently so compartmentalized, crosses over on a night where everyone is happy and drinking. People get to know each other as the night goes on, and I feel, for the first time, like I’m really succeeding in New York.

I’m living the dream. Modest professional success, good friends, and plenty of time and opportunity to explore and engage the city. 30 is a winning number.

December 2008 – I’ve been out of work for a few weeks, having lost my job right before Thanksgiving. I’m so focused on getting back into an office that it isn’t until I’m having drinks with a professional contact that another way is apparent to me. Why don’t I consult, she asks? Why don’t I use my knowledge and experience as a freelancer? We discuss it further, knocking back whiskeys and talking personal branding and business strategy.

As Christmas approaches, I know I have a difficult conversation to have with my girlfriend. She’s in grad school and I’m paying the majority of our rent and bills. But will she be willing and able to support me taking a risk? To help me build a business in New York?

July 2009 – The six-month contract with my biggest freelance client is nearing a close. They make me an offer. I can come on board full-time or I can train someone to do my job internally. Either way, my consulting gig with them is coming to an end. The offer is low. My instinct is to walk away from it and continue to focus on building my business with other clients. I’ve had a lot of meetings recently, written a slew of proposals. But there is an air of uncertainty. The recession is still pretty new and nobody knows where the economy will go.

I can’t make the decision alone. Not when I’m responsible for more than myself. Ultimately, I’m convinced to ignore my instinct in favor of stability. It feels like a mistake from the moment I accept the job, which never bodes well. But sometimes we make decisions based on need. Or fear of uncertainty. Despite the best intentions of everyone involved, it’s a bad idea. Within weeks of taking the position, four different companies I’d pitched get back to me about proposals they’d been mulling over. They all want to work with me and I’m locked into a full-time position. I curse myself for choosing fear.

September 2010 – I stand at a crossroads. As the end of another contract approaches, I have nothing in particular on the horizon. Single for the first time in over two years, I have nothing holding me in place. I love New York, but I realize that I can do anything I want. Go anywhere I want. I have the kind of freedom that doesn’t often come around and I should really take advantage of it.

So I do. I pack up everything I own, so much more than the things I could carry with me five years prior, and I put it all into storage in a friend’s garage out in Long Island. Two days after my gig ends, I hit the road. I spend seven weeks traveling the country by train, exploring, flirting with other cities behind New York’s back.

November 2011 – After a year of living in Los Angeles, I return home to New York, just in time for the bitter cold of winter. I’m freelancing full-time, but all of my clients are on the west coast, so I’m keeping odd hours.

A friend in the Bronx was looking for a roommate around when I was looking to return to New York, so I find myself in a neighborhood I don’t quite fit in, missing many of the creature comforts I associated with my New York experience, and having to take the train 45 minutes to an hour for any kind of social life. It’s a tough adjustment.

February 2012 – I’m working seven days a week on a big community management project. I haven’t taken a full day off since Christmas and it’s taking its toll. I’m missing the camaraderie of an office. Hell, the change of scenery alone would be amazing. Every day I wake up and fire up the laptop. I’m working before I have a drop of caffeine. I’m usually putting the last touches on things before I fall asleep at night.

For two months I see very little beyond my computer and Parkchester. It’s an isolating experience, something I could do anywhere. I don’t feel connected to the city. I don’t feel connected to my life. I need to find a balance point in my life, location, and job.

May 2013 – My hunt for work, freelance or full-time is at a fevered pitch. I’ve reorganized my resume as an infographic, I’ve adopted new strategies in personal branding. I feel reinvigorated, rising to the new challenges of the job market, determined to succeed.

I’m about to move to Brooklyn with my girlfriend. The thought of it makes me obnoxiously happy. She loves the city like I do. We find the same manic joy out of discovering something new here. We love local beers and neighborhood restaurants. We love just walking through the city until our feet hurt. I get to share New York with her! How awesome is that? What’s more, she believes in me, something that is crucial in a partner when you’re attempting to redefine your career.

Once more I find myself at a crossroads. I’m excited for what the future holds.